Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/12—Preparations containing hair conditioners
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents

Definitions

• This invention relates to a novel fatty acid-lactic acid ester and, more particularly, to a lactic acid ester of ⁇ -branched fatty acid which possesses an excellent hair conditioning effect and can be used as toiletries.
• lactic acid esters of fatty acids function to produce an antiseptic effect, emulsion formation, detergency, and the like, and can be absorbed by proteins, they are used in foods, shampoos, cosmetics, or the like.
• Stearoyl lactic acid salts sodium or potassium salt which are linear fatty acid esters, for example, are known to be capable of ensuring soft-baked bread, and of providing an anti-aging effect. These compounds are used as a bread substrate improver.
• lactic acid esters of a linear fatty acid In addition to these lactic acid esters of a linear fatty acid, lactic acid esters having an acyl group of iso-stearic acid with a methyl group as a branched chain, which are produced as by-products in the production of dimer acids, are also used for shampoos and cosmetics as agents producing the effects of detergency, emulsification, and conditioning.
• lactic acid ester of iso-stearic acid which is a by-product of dimer acid production processes, or the like
• hair cosmetics such as shampoos and rinse
• the conditioning effect of these esters is not yet satisfactory in view of the tangling feeling when hair is combed or an incompletely finished feeling after washing due to the absence of dampishness.
• an object of this invention is to provide a fatty acid-lactic acid ester represented by the formula: ##STR1## which R 1 and R 2 independently represent alkyl groups of a C 4-18 carbon atom content, X represents a hydrogen atom, alkali metal, alkaline earth metal, ammonium group, alkanol ammonium group, or lower alkyl ammonium group, and n represents a value of 1 to 5.
• Another object of the invention is to provide a shampoo composition
• a shampoo composition comprising as essential components the fatty acid-lactic acid ester of the above formula (I) and an anionic surface active agent.
• Still another object of the invention is to provide a rinse composition comprising as essential components the fatty acid-lactic acid ester of the above formula (I) and a quarternary ammonium salt.
• the acyl group of ##STR2## may be 2-butyloctanoyl group, 2-butyltetradecanoyl group, 2-hexyldecanoyl group, 2-heptylundecanoyl group, 2-octyldecanoyl group, 2-decyltetradecanoyl group, 2-decyloctadecanoyl group, 2-tetradecyloctadecanoyl group, 2-hexadecyleicosanoyl group, or the like.
• those containing 14 to 32 carbon atoms are preferable.
• particularly preferable fatty acid-lactic acid esters are those containing an acyl group of the formula: ##STR3## in which n has a value of 5 to 15 and m has a value of 3 to 14.
• n value in formula (I) represents the average numbers of lactic radicals --OCHCH 3 CO--, and is preferably 1 to 3.
• Fatty acid-lactic acid esters of this invention can be prepared according to methods known in the art. For example, they are easily prepared by reacting a fatty acid of a suitable structure and carbon atom content with lactic acid in the presence of an alkali such as sodium hydroxide, potassium hydroxide, sodium carbonate, or the like, at 140 to 220° C. for 4 to 10 hours while eliminating formed water, and, as required, by converting the free acids thus obtained into various kinds of salts. In this reaction, an n mole amount of lactic acid [n is the number in formula (I)] is charged to the reaction system and reacted with one mole of fatty acid, using usually an alkali of one mole.
• an alkali such as sodium hydroxide, potassium hydroxide, sodium carbonate, or the like
• a 50% or 90% aqueous lactic acid solution available in the market may be used as a starting raw material for this reaction.
• Such an aqueous lactic acid solution if heated to a temperature of 180° C. to 220° C., is readily converted by dehydration-condensation to condensed lactic acid.
• condensed lactic acid can also be used as a raw material.
• fatty acids which are another starting raw material for deriving the esters of this invention
• commercially available fatty acids can be used such as, for example, 2-heptylundecanoic acid (Trade Name: Diadol 18GA, manufactured by Mitsubishi Chemical Industries, Ltd.) which is obtained by oxidation of Guerbet alcohol, 2-(1,3,3-trimethylbutyl)-5,7,7-trimethyloctanoic acid (Tradename: Iso-stearic acid, manufactured by Nissan Chemical Co., Ltd.) derived by oxidation of an aldol condensate, and the like.
• Fatty acids to be used are not limited to those mentioned above.
• Various fatty acids with a variety of carbon atom contents and prepared by diversified methods can be used as raw materials.
• the fatty acid-lactic acid esters of this invention can be formulated in shampoo compositions and hair rinse compositions. Examples of preferred formulations are as follows:
• anionic surface active agents to be used as component (B) of these compositions are salts of alkylbenzene sulfonic acids having alkyl groups of an average 10 to 16 carbon atom content, salts of sulfuric acid esters of higher alcohols having an average 8 to 18 carbon atom content, salts of sulfuric acid esters of polyoxyalkylene (an average 1 to 10 mole adduct of C 2 or C 3 alkylene oxide) adducts of higher alcohols having an average 8 to 18 carbon atom content, salts of ⁇ -olefin sulfonates with an average 8 to 18 carbonatom content, salts of alkyl phosphates with an average 8 to 18 carbon atom content, and the like.
• a counter ion of these anionic surface active agents is selected from the group consisting of alkali metals, alkaline earth metals, ammonium, and alkanol amines of a C 2 or C 3 carbon atom content.
• Known components for conventional shampoos may be formulated in the shampoo compositions of this invention as required in the amount not impairing the effect of this invention.
• Such known components include, for example, amphoteric or nonionic surface active agents, solubilizing agents such as propylene glycol, glycerol, urea, and the like, viscosity controlling agents such as ethyl alcohol, isopropyl alcohol, hydroxyethyl cellulose, methyl cellulose, higher alcohols, and the like, perfumes, coloring agents, ultraviolet absorbers, antioxidants, antiseptics, pearly agents, and the like.
• Preferable salts of quaternary ammonium to be used as the component (C) are compounds represented by formula (II): ##STR4## which one or two radicals among from R 3 -R 6 represent long-chained alkyl or hydroxyalkyl groups each having 8 to 22 carbon atoms, with the remaining radicals being alkyl or hydroxyalkyl groups each having 1 to 3 carbon atoms, or benzyl groups, and X represents a halogen atom or an alkyl sulfate group of a 1 or 2 carbon atom content.
• Various additives commonly used for hair treatment agents may be added to this hair rinse composition to the extent that its intended effect may not be impaired.
• Such additives include oils or fats such as fatty acids, higher alcohol, oil or fat esters of lanolin, liquid paraffin, and the like, surface active agents such as nonionic surface active agents, amphoteric surface active agents, and the like, disinfectants, vehicles, perfumes, coloring agents, and the like.
• surface active agents such as nonionic surface active agents, amphoteric surface active agents, and the like
• disinfectants, vehicles, perfumes, coloring agents, and the like disinfectants, vehicles, perfumes, coloring agents, and the like.
• hydrocarbons with molecular weights of 100 to 700, such as liquid and solid paraffin, in the amount of 0.1 to 10% will enhance softness of hair treated by these hair rinse compositions.
• Fatty acid-lactic acid esters prepared as illustrated above not only possess excellent dehydration resistance in themselves, but also, when applied to hair or skin, produce an easiness or readiness of handling, and improve such conditioning effects as slipperiness and hair curling formation or retention performance.
• the compounds of this invention therefore, may find wide application in the toiletry field as ingredients for shampoos, rinses, treatments, creams, and the like.
• the shampoo compositions in Table 3 were prepared according to a conventional method. Each shampoo composition was subjected to testing, in which human hair weighing 30 gm retaining 20 gm of water at 40° C. therein was washed with 1 gm of the shampoo composition. Lathering, cleansing ability, and the like of the composition were evaluated by expert panelists. The results are shown in Table 3. In this test, the following standards were applied to the composition evaluation.
• DDD slipperiness of lather is inadequate causing the hair to tangle around the fingers and be brittle.
• AAA lather is abundant and creamy
• CCC the amount of lather is adequate, but lather is coarse
• Hair rinse compositions of formulations shown in Table 6 were prepared. Hair bundles each weighing 30 gm were washed using a plane shampoo and rinsed in the same manner as in Example 8. To each hair bundle the hair rinse compositions of 1 gm each were applied, which was rinsed again, and dried. Each bundle was subjected to organoleptic evaluation to determine product satisfaction by expert panelist. The results shown in Table 6 were obtained using the following standards for evaluating the compositions.

Landscapes

• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Chemical & Material Sciences (AREA)
• Materials Engineering (AREA)
• Engineering & Computer Science (AREA)
• Organic Chemistry (AREA)
• Dermatology (AREA)
• Emergency Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Cosmetics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Detergent Compositions (AREA)
• Fats And Perfumes (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=12305917

Family Applications (1)

Country Status (10)

Cited By (14)

Families Citing this family (12)

Citations (8)

Family Cites Families (4)

• 1988
  • 1988-01-11 JP JP63003298A patent/JPH0625090B2/ja not_active Expired - Fee Related
  • 1988-02-02 EP EP88101490A patent/EP0278370B1/de not_active Expired - Lifetime
  • 1988-02-02 ES ES198888101490T patent/ES2038701T3/es not_active Expired - Lifetime
  • 1988-02-02 DE DE8888101490T patent/DE3867246D1/de not_active Expired - Fee Related
  • 1988-02-02 AT AT88101490T patent/ATE71082T1/de active
  • 1988-02-05 MY MYPI88000116A patent/MY100861A/en unknown
  • 1988-02-05 US US07/152,493 patent/US4846991A/en not_active Expired - Lifetime
  • 1988-02-11 PH PH36486A patent/PH25239A/en unknown
• 1993
  • 1993-05-28 SG SG705/93A patent/SG70593G/en unknown
  • 1993-09-30 HK HK1034/93A patent/HK103493A/en not_active IP Right Cessation

Patent Citations (8)

Also Published As

Similar Documents

Legal Events